Phosphorus oxychloride → 5-Chloro-1,6-naphthyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 1,6-naphthyridin-5(6H)-one (500 mg, 3.42 mmol) in POCl3 (10 mL) was stirred at 100° C. for 14 h. POCl3 was removed under reduced pressure. The residue was dissolved with DCM (40 mL), and the solution was stirred at 0° C. Then aqueous Na2CO3 was added cautiously to adjust pH to 6-7. Then the organic phase was separated from the aqueous phase, and the aqueous phase was extracted with EtOAc (4×15 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 5-chloro-1,6-naphthyridine as a yellow solid (533 mg, yield 95%). ESI MS: m/z 165 [M+H]+.

Provenance & Evidence